What The HELL Was I Thinking?
by love14
Summary: As Dean goes through the memories he has of Lisa and Ben. He asks himself one question: What the HELL was I thinking? Not because he didn't want to be there but because he did. Trying to separate two lives is not as simple as he thought.
1. To Live Free and TwiHard

**Author's note: Hi everyone! This is my first fanfiction ever! I was inspired and I just wanted to share with all you veterans what was in the inner works of my head! I absolutely love Dean and I thought I might do him some justice. He has been going through hell (figuratively) and I wanted to share my take on it all. P.S. Love, Love Lisa and Ben! **

**Any and all criticism is appreciate! Please, Please, Please don't be shy to hit that review button at the bottom either ;) Thanks much love, Alisha! Miss love14**

**Disclaimer: I do not own anything nor do I wish to step on any toes! So enjoy!**

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><p>Living the life that I live, it was foolish of me to think that I could lead an "apple-pie" life. My job is to HUNT and KILL all the things that go bump in the night. I tried to tell her. To think that it would be a good idea to come to see her. To say good-bye; while I was in transition from that GOD damn vampire!<p>

As I stood by our bed and watched as she whipped her tiered filled eyes. All I could think about was the smell of her blood calling to me. She was so beautiful.

"Ah hey I wasn't expecting to see you for a couple of days." She reached over to the bed side table to turn on the lamp. I had the urge to shield my eyes from the penetrating light. But I winced instead.

"Yeah I ah I wanted to see you." I said as I was walking towards her to sit on the foot of the bed.

"What's up?" Still squinting from the light illuminating from the lamp I gave her a sideways glance. "Are you ok?"

"Listen…" Lisa moved to sit closer to me, alarmed at the gruff tone in my voice.

"What's going on?"

"It doesn't matter." I looked at her. "But I need you to know, you and Ben…" and at that moment she knew that before he finished his sentence this was a Dean Winchester good-bye. As I looked away to finish my sentence I said "Just ah, thanks." I turned to look her in the eyes so she knew that I meant every word. "Ok for everything." I needed her to hear the conviction in my voice.

Lisa pulled the cover from her legs and slides her body closer to mine.

"Dean you're scaring me."

It wasn't bad enough that I had the balls to show up. She had to look.. Well there were no words to describe my "Jumby Girl" tonight. The smell of her had me feeling like that whiny ass, excuse of a vampire Edward friggin' Cullen. I abruptly stood up and walked.

"Oh God I'm Pattinson!"

"What?" she asked confused. I took a breathe and turned to look at her. " Nothing I-I-I got to go."

I knew when I said that she was going to try and stop me. Ask all the questions that NEEDED to be answered. She throw the bed spread from her legs and jumped to a standing postion and walked towards me.

"No. No you can't just show up here like this and then…"

"Believe me I wish it was different." This is me grasping at straws.

"Yeah. Just stop, and explain to me what is going on out there!"I knew she was upset I didn't blame her I always seem to be doing this to her. Telling her something cryptic and then saying that I have to leave before it gets to serious. This time was different. I could hear my heart beating a mile a minute. I could feel the blood rushing through her veins. It was deafening. I was grimacing at this point.

"Lis I can't want to bring this crap home to you**." **In that moment with her looking at me with those big brown eyes I knew that at that moment this was a bad idea.

"You're talking about you're work?" If only it were that simple.

"I'm talking about my life…it's ugly and it's violent. And I am going to _die _soon!" I didn't know how else to explain this to her. I don't think that I have ever been more vulnerable with a women then I was when I was with her. To see her the questions building behind her eyes I knew that I didn't have enough time.

"Just tell _me_." Her voice was shivering with fear and her eyes… her eyes. She grabbed hold of my arms and demanded an answer. "Just tell me what the hell is going on." Her eyes roamed my face. I was staring back at her but all I could hear was the pounding of her heart and I was trying to my cool but it slipped.

I took hold of her arms and backed her into the nearest wall to us. As I did this I heard her gasp. I could see the confusion in her eyes. She was breathing heavily and I could feel the heat of it on my cheek. I knew she was thinking I was going to kiss her. Not the way I would have had it not been for this damned vampire shit that consuming me. I couldn't bear the idea of hurting.

As I pulled away from Lisa, I could feel this piercing pain come from my mouth. Then the fangs came out and I gasped.

"Dean?"

"I got to go." This time there was no room for discussion. I wasn't risking it. I pulled our bedroom door open and walked into the hallway. Shielding my mouth with the arm shelve of my jacket, I could hear Ben's feet shuffling in his room. As I walked toward his room I prayed to God himself to not let him open his door. Do you think He would listen? Hell no! Just as I was approaching his door, Ben opened it and the light coming from his room spilled into the hallway. Blinding me; He was rubbing the sleep from his eyes, disorientated. Then he realized it was me.

"Dean?" He had the biggest smile on his face.

"Ben just _stay_ there!" Do you think that this one time that I ask this kid to do something he would do it? No. He continued to walk towards me.

"I thought I heard you…" I had to push him away from me and as I heard his little body make contact with the wall I stumbled against the wall closest to me and I saw Lisa standing in the door way horrified. Had it not been for this I never would have laid a hand on Ben. Putting my arm to my mouth again, I began to run down the hall.

That was the moment I knew that things were going to be different. I was never going to have the right words to say to explain to her how sorry I was for this. I just hoped I didn't royally screw everything up.

I'm a Winchester.

What the **HELL** was I thinking?

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><p><strong> Thank you so much for reading! No worries I have more up my shelve. This has officially become my baby :)<strong>


	2. You Can't Handle The Truth

**Author's note: Hi everyone! This is my first fanfiction ever! I was inspired and I just wanted to share with all you veterans what was in the inner works of my head! I absolutely love Dean and I thought I might do him some justice. He has been going through hell (figuratively) and I wanted to share my take on it all. P.S. Love, Love Lisa and Ben! **

**Any and all criticism is appreciate! ****J****Please, Please, Please don't be shy to hit that review button at the bottom either ;) Thanks much love, Alisha!**

**Disclaimer: I do not own anything nor do I wish to step on any toes! So enjoy!**

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><p>You Can't Handle The Truth.<p>

As I pulled up to Carlton Court I heard my phone ring. I turned off the engine. As I looked down at the screen I saw her name. God if it didn't come at the worst possible time! I opened the car door and stepped out. _. _I pushed talk.

"Hey."

"_So I saw you called."_ I knew that tone. It's the "I-am-pissed-at-you tone. Trust me Lis got that one down pat.

Nodding my head as if she could see me. "Yeah. It's been crazy." I walked toward the passenger side of the car.

"_Ben won't even talk about it."_ Damn it. I knew that we were going to have to talk about this.

"Lisa I'm sorry but this is actually the worst time in the universe to talk. Can we do this later?" I just hopped that today was not that day.

"_You shoved my kid Dean. How about we do this now?"_

But knowing my luck and the fact that I have been cursed with the damned truth; there is no evading this. I leaned against the door. "It wasn't like that." Damn it!

"_Then how was it?"_

"I can't really explain." I can't explain this to her. I am trying to shield her from this that was the whole point. I could almost imagine her on the other end disappointed in me again. Shaking her head.

"_You want to know the truth?"_ Of course. Talking with Bobby on the phone kinda got me thinking that this wasn't face-to-face specific. This is gonna hurt.

"Probably not." I took a deep breathe to prepare myself.

"_You've got so much buried in there. And you push it down and you push it down. Do you honestly think you can go through life like that and not freak out?" _Here it comes. "_Just what? Drink have a fifth a night and you're __**good**__?_

"Hey you knew what you signed up for."

"_Yeah. But I didn't expect Sam to come back. And I'm glad that he's ok. I am. But the minute he walked through that door I knew it was over!" _

What is there to say to that? I didn't know what to say. Was it truly this hard to be with? Sam and I are NOT normal. Why did I think I could lead a normal life?

"_You two have the most unhealthy, tangled up, crazy thing I have ever seen; and as long as he is in your life you are ever going to be happy."_

Sam and I do have a twisted and complex relationship. It comes with the territory. When your life is constantly hung in the balance, and you literally have dodged your fate and DEATH, countless times; the brother-brother relationship is bound to be intense and all consuming. Because in my life we ARE all each other have. God damn yellow eyes made sure of that.

I have sacrificed a lot for him. Peace and Freedom. Just like Cas said. What would I rather? At this point I don't have a clue. All I know is that I want both lives. The one with Sam were we're kicking serious ass and "making a difference." But I also want this life. With Lisa and Ben. The one were there isn't death at my door every day. The one where I _am _the construction worker, the lover, and father that I _wish_ I could be. There isn't anything that I wouldn't give for it. Baseball games. Movie night. Late night dinners The whole thing.

"_That came out so much harsher then I meant" _I could hear how stunned she was.

"It's not your fault." I said softly as a sad smile graces my lips.

'_I'm not saying be close to Sam. I'm close to my sister." _At this point I closed my eyes . _"But if she got killed. I wouldn't bring her back from the dead." _ It wasn't so much that I didn't want to hear what she had to say. It was that it was true. She was right.

"Okay. Lis? I'm not gonna lie. Ok me and Sam we…" I shrugged my shoulders and pursed my lips. "Got issues no doubt. But you and Ben…"

_"Me and Ben can't be in this with you. I'm sorry."_

I know that she was. When she hung up, I looked back at the phone In utter defeat. I have been pushed to the max emotionally. Lisa and Ben were my light in the dark and cold that was left of my tattered soul. I scuffed. This is my own personal hell. I knew it wasn't gonna be easy.

What The HELL Was I Thinking?

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><p><strong>Feel free to review! :) Thanks for reading!<strong>


	3. 99 Problems

99 Problems

Even in leaving and distancing myself from that life that I really wanted; it was inevitable that it was all going to blow up in my face. I mean with Sam back in my life I have all that I need. He is my responsibility AFTER ALL. Lisa had a point. I don't think that I will ever be **truly** happy. But I sacrificed happiness to kill the sons-a-bitches that I kill on regular basis. On occasion I do help better the lives of the victims that succumb to the evils of the night.

Think that even if Sam had not returned I would have been haunted by my past. Who am I kidding there is no such thing as _past. _In my life there is a thin line that blurs past, present and future.

I was there because HE asked me to be. What was it he sad again. Oh right

_"You go find Lisa. You pray to God that she's dumb enough to take you in. You have barbeques, and go to football games. You go live some normal apple pie life Dean. Promise me! _ He said.

What was I gonna do? Not go? Because as much as I wanted to go and lock myself away in an empty hotel room that smelled like dirty sheets and was definitely not healthy by any means. I knew that going into a drunken a coma was not the answer. So yeah, I knocked on Lisa's door. For what I had hoped was the last time.

Thinking back to the last time I had done this, I was here to tell her goodbye. For good.

_Knock, knock._

_Lisa opened her front door. As she did I was stunned she looked even more beautiful then she had two years ago. I could tell by the look on her face that she was more than shocked to see me on her front door step. Again. _

_"Dean."_

_"Hey Lisa." I smiled at her and shrugged. "I didn't have your number so..."_

_"Yeah. No it's okay. I just um. Just surprised." That was definitely an understatement._

_I let out a breath and smiled. "How's Ben?"_

_"Good, good. He's at baseball." Well. Hmm of course. Because I didn't have this fantasy in my mind's eye before. _

_"Hmm... You moved that's umm. Nice house." Okay I think that my avoidance skills are making e look like a complete idiot right now. But for some reason I knew that she would catch on. I really didn't want to have to just come out and say it. _

_"Dean you didn't come all the way out here to talk about real estate." No I didn't I came here to let out for you tell you everything because at the end of this conversation I am going to say yes to Michael. Be that frickin vessels that I am "destined" to be and I will never see you again._

_"You alright?" I scuffed at that. I looked back at her. I had a storm behind my eyes and I wanted to let her know that what I am about to say is the whole-hearted truth._

_"No. Not really." I looked down shaking my head from side to side._

_"What is it?"_

_I looked back up at her and it was time to lay it out on the line. "Look I have no illusion. Ok. I know that the life that I live... i know how that is going to end for me. Whatever. I'm ok with that. But i just wanted you to know. That when I do picture myself happy it's with you...and the kid." _

_I couldn't help it. All the things that I had sacrificed so that others could lead a "normal" life had me fighting back tears. I gave her a sad smile. The pause after that. Me pouring my heart out to her was not something I do very often. Forget that. Ever. If I was going to face rejection now was the best to that. I mean I really don't have anything left to live for._

_"Wow."_

_"You don't have to say anything." i shock my head still looking down I really didn't want to see the look on her face._

_"No-I...I mean I know. I know" That has me throw my head up and look her directly in the eye. "I want to." She smiled at me and I crumbled. _

_"Come inside let me get you a beer." As she turned to go I had to stop her._

_"I wish I could." As turned to look at me her smile faltering. I was searching her I eyes. For what I don' know but **damn-it! **I had come to what I had come to do and now it was time to go and meet my impending fate. _

_"Take care of yourself Lisa." i whispered as I turned to walk away. I should have known she was going to let me get off that easy._

_"No. No. Wait." Then I felt her small hand tug on my arm. I closed my eyes and took in a deep breathe. _

_"You can't just drop a bombshell like that and then leave!" I half turned toward her._

_"I know. I'm sorry. But I don't have a choice." Now facing her I didn't want it to be like this I wanted more than anything to take her up on that beer. Go inside and pretend for a minute that everything was going to be alright. But it wasn't and I was going to be on the receiving end of it._

_"You do. You do. You can come inside and let me get you a beer. And we can talk." She was so earnest. It only made it hurt more. I didn't want it to come to this. I grabbed her arm to stop her from going inside._

_"Lisa wait a minute." she stopped and she that stubborn look on her face. I had to let her know what was coming her way. The reason. Or as close to the truth as I could get._

_"Things are about to get really bad." Then she took her arm from my grasp and folded her arms in a defensive manner. As if to protect herself from what I was about to unleash on to her._

_"Like how? Like your kinda bad?"_

_"Worse. The next few days of crap you're gonna see on TV is going to be downright trippy. Scary. But I don't want you to worry, because I am making arrangements for you and Ben."_

_"Arrangements?"_

_"Whatever happens you're gonna be ok."_

_"What do you mean? What are you talking about?" Here come the questions that I was I had the time to answer._

_"The people that I am going to see next; they're not going to get a thing from me without agreeing to a few conditions." Her eyes were trained on my face. I knew that it was a lot to take in but I had to let her know._

_"Just come inside. Please." She was pleading with me now. As she grabbed hold of my hand and had it between both of hers. "And whatever you're thinking of doing don't do it." I clasped on to her hand s and was rubbing them with my thumbs. _

_"I have to."_

_"Just stay an hour. At least say bye to Ben." I wish I could. **Damn-it! **Her eyes were glazed with tears and I was beginning to lose my composure. I looked down thinking about the first time I laid eyes on him. He looked just like me and he had that bravado of the "lady's man" just like me. I am really going to miss that kid._

_"Naw. It's better if I don't." She shook her head once and she accepted it. Not because she wanted to but because I wasn't leaving any more room for discussion. I shook my head and as I looked at her devastated face I was think of all the ways I could make this up to her. I didn't want to leave. But I had no choice. My life... I didn't have the time for... what am I talking about. I need these women. There is no way around it. I know that I am disappointing her right now but I know that she can deal with it. At least I hope so. She doesn't deserve this. She deserves much better than me. _

_So I brushed her hair from her cheek and she closed her eyes just slightly as I reached over and kissed her cheek. Trying to convey how sorry I was that I was doing this to her. That I basically told her that I loved her but that I had to leave her and Ben for what, that this very moment is forever. _

_She had a tear rolling down her cheek then. _

_"Goodbye Lisa." I was walking toward the Impala sealing my fate._

What The HELL Was I Thinking?


	4. Swan Song

**Hi there everyone! I know that I have been leaving you hanging for a while but I have come out of hiding and put this up! **

**Disclaimer: All characters and all that good stuff belong to the wonderful Eric Kripke and thank you to the wonderful writers of this show because without you there is no basis for this stuff!**

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><p>Swan Song<p>

_You know as I was standing in that cemetery in Lawrence I wasn't thinking that I was going to save Sam. I was there to die with him. Be there until the very end. As I tried to talk to Sam/Lucifer He wasn't too happy about that. Quite frankly he was annoyed._

"_You know. I have tried to be nice." He started to walk toward me. "For Sammie's sake, but you are such a **pain **in my ass." He grabbed hold of the lapels of Dad's leather jacket and flung me straight onto the roof of the Impala; cracking the back of my head off the wind shield. That had me seeing stars. It took me a second to catch my bearings. _

_As he was walking forward I heard a gun fire. It was Bobby. He clipped Sam/Lucifer in the left shoulder and as he turned toward Bobby he fired off another round; straight through his heart. He looked down to the gapping whole in his chest and back up to Bobby's face. I Looked at Bobby and he had that "It was worth a shot" look on his as he shrugged his shoulder. Lucifer/Sam raised his left hand and twisted it as Bobby's neck snapped and he dropped to the ground like a sack of potatoes. _

"_NO!" I screamed. This wasn't happening. _

_He turned toward me and said "YES." He grabbed my left leg and dragged me toward him and gave me his right hook. I was in shock my body just shut down. The blood pouring from my mouth didn't phase me. I was here for a reason. I turned around to look at him._

"_Sammie? Are you in there?"_

"_Oh. He's in here alright." He pulled his left arm back again and his fist barrled on through and connected with my face again. The sheer force had me staggering on to the Impala for support._

"_Ughh."_

"_And he is going to feel the snap of your bones." Bam. That last hit had me on the ground. "Every single one." He picked me and pinned me to the side of the car. "We're going to take our time." Bam, bam, bam, bam, bam, bam, bam, bam." My jaw was numb. I reached out for Sam. _

"_Sam it's okay. It's okay. I'm here. I'm here." I looked into his eyes, searching and hoping that he could hear me in there. "I'm not going to leave you." Bam. Bam. "I'm NOT going to leave you!"_

_As I lay there pressed up against my car and Sam/Lucifer pounding my face all I could think about was how I wanted it to be over. For Lucifer to beat me to death, so that I didn't have to witness Michael/Adam and Lucifer/Sam fight to the death. At least this way if Sam is the one that dies according to the "prophecy" and all that other bullshit those god-damn angles say I will be gone to. _

_I have dodged one to many bullets. I started this whole thing! I broke the first; I was the righteous man that spilled blood in Hell and for that, I am paying with what is left of my life._

_If you can even call it that. _

_I was getting prepared for another blow as he raised his right hand to hit me his left held dad's jacket. Then all of a sudden he had this spaced look on his face. As if he wasn't there anymore. Like his mind was somewhere else. He slowly unclenched his fist and let go of his firm hold on me. He staggered back and he grunted. He was breathing heavy. I lolled my head in his direction and as we locked eyes I knew it was "my" Sam._

"_It's okay Dean. It's gonna be okay. I've got him." Still breathing heavy Sam reached into his front jeans pocket and pulled out the Horsemen's Rings. He threw them at the ground and began chanting. Then the ground began to implode onto itself and the wind began to whirl as the hole began to suck it down under. Sam and I looked at one another. I could tell that he was terrified, hell so was I. I saw his goodbye in his eyes. He was scarred he was taking deep greedy breathes to prepare himself for the plunge. No amount of breathes was going to end this. _

"_Sam!" It was Michael. _

_Sam turned his head toward his voice stunned. I guess Cas was right. It was only going to stall him for a bit. _

"_It's not going to end this way! Step back!" his voice was raised to compete with the howling wind._

'_You're gonna have to make me!"_

"_I have to fight my brother Sam! Here and now! It's my DESTINY!"_

_I watched as Michael tried to convince Sam to stay put. Sam wasn't hearing it. We had our final goodbye in a single glance. As he reached down within his soul to fight off Lucifer and he closed his eyes ready to jump in the hole. I could hear Michael scream "No" in the distance. But I couldn't take my eyes off of Sam. As Michael rushed toward him Sam took pulled him into the hole and they fell. _

_Together._

_That hole reformed and a bright white light flashed before my eyes as tried to shield them. I lay there with my back against the car in utter defeat. It was over and I couldn't breathe. Sam was in the fucking cage! And there was nothing I could do about it. I could feel my throat closing and the tears welling n my eyes. _

_Cas._

_Bobby._

_Sam._

_They were all gone and I was left here all alone. I was on my knees at the hole that is no longer there and picked up the rings. I felt a presence behind me then. I turned my mangled face toward it. _

"_Cas. You're alive?" He put two fingers to my forehead and the pain that I felt in my broken cheekbones and eye socket were gone. I was looking around hoping that this wasn't a dream. _

"_Cas are you God?" That was the only way I could explain the new super powers._

"_That's a nice compliment. But no, although I do believe that He brought me back." He turned and walked away. "New and improved."_

_I was still astonished. I reached to touch my face and then I remembered. Bobby. Cas kneeled and did that juju thing he just did to me and Bobby was breathing again. I looked down at my hand and looked at those God damn rings. Hmm now what? _

_Driving away from the cemetery was the hardest thing I think I have had to do in a long time. Losing Sam isn't like losing your wallet or car. It's like losing a friggin limb. He was all I had left in this world. He kept me grounded. It's something in my life that was real. He was my brother.** Is **my brother. Now the question remains. What now? I looked over at Cas and asked him._

"_Return to Heaven I suppose."_

"_Heaven?" Is he frickin' serious right now?_

"_With Michael in the cage I am sure that its total anarchy up there."_

"_So what? You're the new sheriff in town?"_

"_I like that yeah. I suppose I am."_

"_Well God gives you a brand new set of shiny wings and suddenly you're His bitch again." _

"_I don't know what God wants. I don't know if He will even return. I just…it seems like the right thing to do."_

"_Well if you **do** see Him, tell Him that I am coming for Him next."_

"_You're angry."_

"_That's an understatement."_

"_He helped" I scoffed at that bullshit. "Maybe even more then we realize."_

"_Well that's easy for you to say. He brought you back! But what about Sam? What about me? Huh? Where's my grand prize? All I got was my brother in a HOLE!"_

"_You got what you asked for Dean." Excuse me! "No Paradise. No Hell. Just more of the same. I mean it Dean. What would you rather have? Peace or Freedom?_

To this day I ask myself that exact question. Was THIS all worth it? I had to have been for something. If hadn't have been for this I don't think I would have been standing at Lisa's door step again.

Ever. I had no business there. I was there because Sam asked me too. Right?

_It's just Bobby and I now. Once there Bobby knew that I was gonna leave. I told about the promise I had made to Sam and that I intended to keep it. Bobby pulled me into a hug and we said our goodbyes. As I drove off I had it in my mind that I was going to do whatever it took to get Sam back. Or I was going to go on a suicide mission and be one with it. But I can't I had to do one more thing. _

_Knock, knock, knock_

_I could see her then, walking to the door through the window. It almost that evey time I do this she looks surprised to see me. This time It was different. It wasn't that she didn't expect me to be at her door step it was that she was surprised that I was alive. _

_The first thing to come out of her mouth was "Thank God." After all the bullshit that I have been through with that- I can't even be mad right now I am to numb to care. I realized that seeing her face and coming here was the only place I had to go to. The only place that was safe and warm for me to out my head down and forget. _

"_Are you alright?"_

"_Yeah. Umm If it's not too late I think that I'd like to take you up on that beer."_

"_It's never too late." She had a smile on her face then and I was ready to fall apart. She motioned me inside and as I was about to cross that thresh hold I grabbed onto her for dear life. _

"_I lost him." _

"_Shh, shh, shh, shh. It's okay Dean. It's gonna be okay." I wanted to believe her so bad. I couldn't feel it. I could feel her arms wrapped around my neck and I search for solace there. I found it as the flood gates opened and I let it all go. _

I wanted to go to bed that night, wake up to find that day had all been a bad dream.

I'm a Winchester.

What The HELL Was I Thinking?

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><p><strong>Okay guys so I hope that I have done it justice! There a few more to come! Don't be afraid to hit that review button! :) Love Alisha!<strong>


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